Stromeier Stefan, Petereit Frank, Nahrstedt Adolf
Institute of Pharmaceutical Biology and Phytochemistry, Westfälische Wilhelms-Universität, Münster, Germany.
Planta Med. 2005 Jun;71(6):495-500. doi: 10.1055/s-2005-864148.
Five phenylpropanoid esters, caffeoylglycolic acid, 2-caffeoylpiscidic acid (cimicifugic acid D), 3,4-dihydroxyphenacyl caffeate (petasiphenone), 3,4-dihydroxyphenyl-2-oxopropyl isoferulate (cimiciphenol) and 3,4-dihydroxyphenacyl isoferulate (cimiciphenone) were isolated from a commercially available extract of the rhizomes of Cimicifuga racemosa (L.) Nutt. (syn. Actaea racemosa L.) for the first time; the known cimicifugic acids A, B, E, F, fukinolic acid, fukiic acid and caffeic acid were also obtained. Cimiciphenone and caffeoylglycolic acid are new natural products. The structures were elucidated by means of spectroscopic data (ESI-MS, 1H-, 13C-NMR, COSY, HMQC, HMBC and NOE experiments). Ferulic acid and isoferulic acid were detected by HPLC analysis in comparison to standards. The estrogenic activity of the isolated compounds was tested in an estrogen-dependent MCF-7 mamma carcinoma cell line; 17beta-estradiol (10(-11) M) and the phytoestrogen coumestrol (10(-7) - 10(-5) M) were used as references. The results suggest that, in contrast to an earlier report, the phenolic esters do not exert a proliferative (estrogenic) effect in this test system.
首次从市售的总状升麻(L.)Nutt.(syn. Actaea racemosa L.)根茎提取物中分离出五种苯丙素酯,即咖啡酰乙醇酸、2-咖啡酰水苏酸(升麻酸D)、3,4-二羟基苯甲酰咖啡酸(蜂斗菜酚酮)、3,4-二羟基苯基-2-氧代丙基异阿魏酸酯(升麻酚)和3,4-二羟基苯甲酰异阿魏酸酯(升麻酚酮);还得到了已知的升麻酸A、B、E、F、蜂斗菜醇酸、蜂斗菜酸和咖啡酸。升麻酚酮和咖啡酰乙醇酸是新的天然产物。通过光谱数据(电喷雾电离质谱、¹H-、¹³C-核磁共振、化学全相关谱、异核多量子相干谱、异核多键相关谱和核Overhauser效应实验)阐明了其结构。通过高效液相色谱分析并与标准品比较检测到了阿魏酸和异阿魏酸。在雌激素依赖的MCF-7乳腺癌细胞系中测试了分离出的化合物的雌激素活性;以17β-雌二醇(10⁻¹¹ M)和植物雌激素香豆雌酚(10⁻⁷ - 10⁻⁵ M)作为对照。结果表明,与早期报告相反,在该测试系统中酚酯未发挥增殖(雌激素)作用。